Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/72—Hydrazones
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
  • D06L4/60—Optical bleaching or brightening
  • D06L4/657—Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing

Definitions

• R" is R or (CH -CH 0H; n is an integer from 2 to 4; and A is an anion of an acid.
• Optical brighteners from the class of 1,3-diarylpyrazoline compounds are known which are suitable for the optical brightening of wool and synthetic fibers, especially polyamide fibers.
• a disadvantage of these brightening agents is that they are only relatively poorly absorbed on fibers consisting of chemically modified, or cross-linked cellulose, or on mixed fabrics from polymer fibers and cellulose and, therefore, only eifect a small improvement of the whiteness value.
• An object of the present invention is the obtaining of an optical brightener for textiles having the formula II /N Y/ ⁇ N wherein Y' is H, -R or phenyl;
• Z is H or Y
• Z is H or R R is alkyl having 1 to 4 carbon atoms; R is H or R;
• n is an integer from 2 to 4.
• A- is an anion of an acid.
• Another object of the present invention is the development of a process for the production of the above optical brightener for textiles.
• Preferred optical brighteners are those of Formula I and especially those of Formula II R represents an alkyl residue with 1 to 3 carbon atoms;
• R represents H or R'
• R represents R or (CH CH OH
• n 2 or 3;
• B- is a halide, acetate or alkylsulfate ion or the equivalent of a polyvalent acid, for example, sulfuric, phosphoric, oxalic and citric acids.
• Y as above, represents H, R or phenyl; Z" represents H or Y, and Y represents R being H or R,
• R" being R or (CH CH OH
• n being an integer from 2 to 4, such as derivatives of acrylic, fumaric or maleic acid containing tertiary amino groups with substituted a-halobenzaldehyde phenylhydrazones of the Formula IV wherein X and X have the above-assigned values, and D represents a halogen,
• Suitable derivatives of acrylic acid are for example, compounds of Formula III, wherein Z, Z and Y are hydrogen, and
• Suitable derivatives of fumaric and maleic acid are, for example, compounds of Formula III,
• CHgCHgOH -CO(CH2)2N omcmon such as the amides and esters of the following formulae:
• amides of acrylic, fumaric or maleic acids of diethylenetriamine, its methylation products or its subsequently methylated products, or the corresponding esters with triethanolamine, tripropanolamine and N-hydroxyethyl-N,N,N-trimethy1-ethylenediamine may be used as starting substances.
• the reaction of the aforesaid amides and esters with the substituted u-halobenzaldehyde-phenylhydrazones of Formula IV proceeds smoothly in the presence of an acid acceptor in the direction of a 1,3-dipolar cycle-addition, the hydrazone derivative being first rearranged into a diphenyl-nitrilimine.
• Suitable acid acceptors are, for example, aliphatic or cycloaliphatic primary, secondary and, particularly, tertiary amines, such as trialkylamines, or carbonates, bicarbonates 0r hydroxides of alkali metals or alkaline earth metals.
• the substituted u-halo benzaldehyde-phenylhydrazone of Formula IV is obtainable in known way from the corresponding benzoyl-phenylhydrazine by halogenation, for example, with phosphorus pentachloride.
• substituted benzoyl-phenylhydrazine is prepared in the known manner.
• substituted benzoyl-phenylhydrazines have the Formula V where X and X have the above-identified values.
• reaction of the amide or ester of Formula III with the halogenated hydrazone of Formula IV is suitably carried out with heat in the presence of a solvent, tetrahydrofuran having proved particularly good.
• the substituted diarylpyrazoline can subsequently be converted into the quaternary compound in known way, the usual agents for this purpose being used, such as alkyl halides, dialkyl sulfates or alkyl chlorohydrins, the alkyl residues which contain 1 to 4, preferably 1 to 3, carbon atoms.
• optical brighteners according to the invention are suitable for brightening textiles and other structures containing cellulose, regenerated cellulose and synthetic fibers, and especially those of finished or cross-linked cellulose, and mixed fabrics of cellulose and polypropylene fibers.
• a suitable brightening agent has not previously been known.
• the brighteners may also be used alone or in conjunction with textile washing agents.
• EXAMPLE 2 1.8 gm. (0.125 mol) of p-chlorobenzoyl chloride were dropped into a solution, cooled to +1 C., of 46.8 gm. (0.25 mol) of phenylhydrazine-(4)-sulfonic acid-amide in 250 ml. of anhydrous dimethyl formamide, with stirring and cooling using an ice bath. The mixture was then stirred at +2 C. for a further 4 of an hour and, after removal of the ice bath, was stirred at room temperature for a further 3 hours.
• the crystalline slurry was taken up in 500 ml. of water to remove the phenylhydrazine-(4)-sulfonic acid-amide hydrochloride, and the insoluble p-chloro-B-benzoyl-phenylhydrazinesulfonic acid amide was filtered off by suction, washed twice with cold water and, after drying, recrystallized twice from about 3.5 liters of ethanol.
• the product had a melting point of 267 C.
• 1-p-chlorobenZyl-(2-p-sulfoamidophenylhydrazine)-chloride was obtained in the form of colorless crystals having a melting point of 218 C. to 219 C.
• An optical brightener for textiles having the formula wherein X is a member selected from the group consisting of SO NH SO R, SOg-OR, COOR, CONH CN, CF halogen, OR, and R;
• X is a member selected from the group consisting of halogen, OR and R;
• Y is a member selected from the group consisting of Y is a member selected from the group consisting of H,
• Z is a member selected from the group consisting of H and Z is a member selected from the group consisting of H and is alkyl having 1 to 4 carbon atoms;
• R is a member selected from the group consisting of H and R;
• R" is a member selected from the group consisting of R and (CH CH OH;
• n is an integer from 2 to 4.
• A is an anion of an acid.
• An optical brightener for textiles of claim 1 having the formula wherein X" is a member selected from the group consisting of SO NH COOR and -CONH Y" is a member selected from the group consisting of R is alkyl having 1 to 3 carbon atoms;
• R is a member selected from the group consisting of H and R;
• R" is a member selected from the group consisting of R and m is an integer from 2 to 3;
• B is an anion of an acid selected from the group consisting of a hydrogen halide, acetic acid, sulfuric acid, phosphoric acid, oxalic acid, citric acid and the acid 10 alkylsulfuric acid wherein said alkyl had 1 to 4 carbon
• Cited ii tcal bri ht r f0 textiles of cla'l 2 wh rein UNITED STATES PATENTS H l 1 T1 is 155 x g e s 6 3,141,879 1/1964 Hausennann et a].
• 260-2472 Y LiSAn optical brightener for textiles of claim 3 wherein 5 HENRY R.

Applications Claiming Priority (1)

Publications (1)

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ID=5700635

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Country Status (10)

Cited By (14)

Families Citing this family (4)

• 1968
  • 1968-07-02 DE DE19681770773 patent/DE1770773A1/de active Pending
• 1969
  • 1969-06-04 NL NL6908486A patent/NL6908486A/xx unknown
  • 1969-06-04 SE SE07902/69A patent/SE360361B/xx unknown
  • 1969-06-26 US US836959A patent/US3629241A/en not_active Expired - Lifetime
  • 1969-06-30 BE BE735388D patent/BE735388A/xx unknown
  • 1969-07-01 CH CH1007569A patent/CH554448A/xx unknown
  • 1969-07-01 CH CH1007569D patent/CH1007569A4/xx unknown
  • 1969-07-01 ES ES369025A patent/ES369025A1/es not_active Expired
  • 1969-07-01 AT AT628969A patent/AT294002B/de not_active IP Right Cessation
  • 1969-07-02 GB GB33308/69A patent/GB1242019A/en not_active Expired
  • 1969-07-02 FR FR6922269A patent/FR2012166A1/fr not_active Withdrawn

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